Citric Acid → HCID 178460516, compound

HRID 1713767Notes

Reaction equation

HRID 1713767 reaction equation
C[Si](C)(C)[O-].[K+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[O:20][C:19]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([C@H:30]4[CH2:35][CH2:34][C@H:33]([CH:36]([CH3:42])[C:37]([O:39]CC)=[O:38])[CH2:32][CH2:31]4)=[CH:26][CH:25]=3)=[O:22])=[N:18][N:17]=2)=[CH:11][CH:10]=1)#[N:8].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[O:20][C:19]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([C@H:30]4[CH2:35][CH2:34][C@H:33]([CH:36]([CH3:42])[C:37]([OH:39])=[O:38])[CH2:32][CH2:31]4)=[CH:26][CH:25]=3)=[O:22])=[N:18][N:17]=2)=[CH:11][CH:10]=1)#[N:8]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 23668039Potassium trimethylsilanolateHCID 178471532HCID 178471532, compound

Product 1

HCID 178460516HCID 178460516, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanolate (65 mg, 0.51 mmol) was added in one portion to a solution of trans-ethyl 2-(4-{4-[({5-[(4-cyanophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-phenyl}cyclohexyl)propanoate (Example 583, 25 mg, 0.051 mmol) in THF (2 mL) and the reaction mixture was stirred at room temperature for 48 h. A 1M aqueous solution of citric acid (10 mL) was added and the mixture was filtered to leave a solid. The solid was washed with H2O (2 mL) and purified by reverse phase preparative HPLC, eluting with a gradient of CH3CN and H2O containing 0.2% TFA, to give the title compound (11 mg, 47%) as a solid; 1H NMR δ 1.05 (3H, t), 1.1-1.3 (2H, m), 1.38-1.51 (2H, m), 1.52-1.63 (1H, m), 1.7-1.9 (4H, m), 2.13-2.25 (1H, m), 2.4-2.5 (1H, m), 7.22 (2H, d), 7.7 (2H, d), 7.76 (2H, d), 7.85 (2H, d), 11.0 (1H, s); MS m/e MH+ 460.

Workup

  1. filtrationthe mixture was filtered
  2. customto leave a solid
  3. washThe solid was washed with H2O (2 mL)
  4. custompurified by reverse phase preparative HPLC
  5. washeluting with a gradient of CH3CN and H2O containing 0.2% TFA

Sources & evidence

ORD record
ord-a53be7463baa42a4b40e679a268429d1
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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